US7208510B2 - Fungicidal combinations of active substances - Google Patents

Fungicidal combinations of active substances Download PDF

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US7208510B2
US7208510B2 US11/336,501 US33650106A US7208510B2 US 7208510 B2 US7208510 B2 US 7208510B2 US 33650106 A US33650106 A US 33650106A US 7208510 B2 US7208510 B2 US 7208510B2
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formula
compound
active compound
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weight
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US20060172981A1 (en
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Ulrike Wachendorff-Neumann
Herbert Gayer
Ulrich Heinemann
Thomas Seitz
Bernd-Wieland Krüger
Wolfgang Krämer
Lutz Aβmann
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Bayer AG
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Bayer AG
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring

Definitions

  • the present invention relates to novel active compound combinations which consist of a known fluoro-benzothiazole derivative and further known fungicidally active compounds, and which are highly suitable for controlling phytopathogenic fungi.
  • substituted halogenopyrimidines have fungicidal properties (cf. DE-A1-196 46 407, EP-B-712 396).
  • the fungicidal activity of the active compound combinations according to the invention is considerably higher than the sum of the activities of the individual active compounds.
  • an unforeseeable, true synergistic effect is present, and not just an addition of activities.
  • the product can be present as a mixture of different isomers or else in the form of a single isomer.
  • Preferred compounds of the formula (I) are compounds in which the amino acid moiety is formed from i-propyloxycarbonyl-L-valine and the fluoro-benzothiazoleethylamine moiety is racemic, but has, in particular, the (R) configuration.
  • the formula (II) includes the compounds
  • the formula (IV) includes the aniline derivatives of the formulae
  • the compound has three asymmetrically substituted carbon atoms.
  • the product may therefore be present as a mixture of different isomers, or else in the form of a single component. Particular preference is given to the compounds
  • the formula (VII) includes the compounds
  • the formula (XVI) includes the compounds
  • the compound of the formula (XVII) can be present as methyl N-(2,6-dimethylphenyl)-N-(methoxyacetyl)-DL-alaninate (metalaxyl, XVIIa) or as methyl N-(2,6-dimethylphenyl)-N-(methoxyacetyl)-D-alaninate (metalaxyl-M, XVIIb).
  • hydroxyethyl-triazole derivative of the formula (XXI) can be present in the “thiono” form of the formula
  • the guanidine derivative of the formula (XXV) is a substance mixture with the common name guazatine.
  • the active compound combinations according to the invention comprise at least one active compound of the compounds of groups (1) to (51). Additionally, they may comprise further fungicidally active additives.
  • the synergistic effect is particularly pronounced when the active compounds in the active compound combinations according to the invention are present in certain weight ratios.
  • the weight ratios of the active compounds in the active compound combinations can be varied within a relatively wide range. In general,
  • the active compound combinations according to the invention have very good fungicidal properties and can be employed for controlling phytopathogenic fungi, such as Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes, Deuteromycetes, etc.
  • the active compound combinations according to the invention are particularly suitable for controlling Phytophthora infestans and Plasmopara viticola.
  • the fact that the active compound combinations are well tolerated by plants at the concentrations required for controlling plant diseases permits the treatment of above-ground parts of plants, of propagation stock and seeds, and of the soil.
  • the active compound combinations according to the invention can be employed for foliar application or else as seed dressings.
  • the active compound combinations according to the invention may also be employed to increase the yield of crops. However, they have reduced toxicity and are tolerated well by plants.
  • Plants are to be understood here as meaning all plants and plant populations such as desired and undesired wild plants or crop plants (including naturally occurring crop plants).
  • Crop plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including plant cultivars which can or cannot be protected by plant breeders certificates.
  • Parts of plants are to be understood as meaning all above-ground and below-ground parts and organs of plants, such as shoot, leaf, flower and root, examples which may be mentioned being leaves, needles, stems, trunks, flowers, fruit-bodies, fruits and seeds and also roots, tubers and rhizomes.
  • Parts of plants also include harvested plants and vegetative and generative propagation material, for example seedlings, tubers, rhizomes, cuttings and seeds.
  • the treatment of the plants and parts of plants according to the invention with the active compounds is carried out directly or by action on their environment, habitat or storage area according to customary treatment methods, for example by dipping, spraying, evaporating, atomizing, broadcasting, brushing-on and, in the case of propagation material, in particular in the case of seeds, furthermore by one- or multi-layer coating.
  • the active compound combinations according to the invention can be converted to the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols and microencapsulations in polymeric substances and in coating compositions for seeds, and ULV formulations.
  • customary formulations such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols and microencapsulations in polymeric substances and in coating compositions for seeds, and ULV formulations.
  • formulations are produced in a known manner, for example by mixing the active compounds or active compound combinations with extenders, that is liquid solvents, liquefied gases under pressure, and/or solid carriers, optionally with the use of surfactants, that is emulsifiers and/or dispersants, and/or foam formers.
  • extenders that is liquid solvents, liquefied gases under pressure, and/or solid carriers, optionally with the use of surfactants, that is emulsifiers and/or dispersants, and/or foam formers.
  • surfactants that is emulsifiers and/or dispersants, and/or foam formers.
  • the extender used is water, it is also possible to use, for example, organic solvents as auxiliary solvents.
  • suitable liquid solvents include: aromatics such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, for example petroleum fractions, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulphoxide, or else water.
  • aromatics such as xylene, toluene or alkylnaphthalenes
  • chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride
  • aliphatic hydrocarbons such as cyclohe
  • Liquefied gaseous extenders or carriers are to be understood as meaning liquids which are gaseous at ambient temperature and under atmospheric pressure, for example aerosol propellants such as butane, propane, nitrogen and carbon dioxide.
  • Suitable solid carriers are: for example ground natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals such as finely divided silica, alumina and silicates.
  • Suitable solid carriers for granules are: for example crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, or else synthetic granules of inorganic and organic meals, and granules of organic material such as sawdust, coconut shells, maize cobs and tobacco stalks.
  • Suitable emulsifiers and/or foam formers are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonates, or else protein hydrolysates.
  • Suitable dispersants are: for example lignin-sulphite waste liquors and methylcellulose.
  • Tackifiers such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, or else natural phospholipids such as cephalins and lecithins and synthetic phospholipids can be used in the formulations.
  • Other additives can be mineral and vegetable oils.
  • colorants such as inorganic pigments, for example iron oxide, titanium oxide and Prussian Blue, and organic dyestuffs such as alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
  • inorganic pigments for example iron oxide, titanium oxide and Prussian Blue
  • organic dyestuffs such as alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs
  • trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
  • the formulations generally comprise between 0.1 and 95% by weight of active compounds, preferably between 0.5 and 90%.
  • the active compound combinations according to the invention can also be applied in a mixture with known fungicides, bactericides, acaricides, nematicides or insecticides, to broaden the activity spectrum or to prevent the development of resistance, for example.
  • fungicides bactericides, acaricides, nematicides or insecticides
  • acaricides nematicides or insecticides
  • synergistic effects are obtained, i.e. the activity of the mixture is greater than the activity of the individual components.
  • the active compound combinations can be used as such, in the form of their formulations or as the use forms prepared therefrom, such as ready-to-use solutions, emulsifiable concentrates, emulsions, suspensions, wettable powders, soluble powders and granules. They are used in the customary manner, for example by watering, spraying, atomizing, scattering, spreading, and as a powder for dry seed treatment, a solution for seed treatment, a water-soluble powder for seed treatment, a water-soluble powder for slurry treatment, or by encrusting.
  • the application rates can be varied within a relatively wide range, depending on the kind of application.
  • the application rates of the active compound combination are generally between 0.1 and 10,000 g/ha, preferably between 10 and 1000 g/ha.
  • the application rates of the active compound combination are generally between 0.001 and 50 g per kilogram of seed, preferably between 0.01 and 10 g per kilogram of seed.
  • the application rates of the active compound combination are generally between 0.1 and 10,000 g/ha, preferably between 1 and 5000 g/ha.
  • the good fungicidal activity of the active compound combinations according to the invention is evident from the examples below. While the individual active compounds exhibit weaknesses with regard to the fungicidal activity, the combinations have an activity which exceeds the sum of individual activities.
  • a synergistic effect of fungicides is always present when the fungicidal activity of the active compound combinations exceeds the total of the activities of the active compounds when applied individually.
  • the expected activity for a given combination of two active compounds can be calculated as follows (cf. Colby, S. R., “Calculating Synergistic and Antagonistic Responses of Herbicide Combinations”, Weeds 15, (1967), 20-22):
  • X is the efficacy when applying active compound A at an application rate of m g/ha
  • Y is the efficacy when applying active compound B at an application rate of n g/ha and
  • E is the efficacy when applying the active compounds A and B at an application rate of m and n g/ha,
  • the efficacy is calculated in %. 0% is an efficacy which corresponds to that of the control, whereas an efficacy of 100% means that no infection is observed.
  • the activity of the combination is superadditive, i.e. a synergistic effect exists.
  • the efficacy which was actually observed must be greater than the value for the expected efficacy (E) calculated from the abovementioned formula.
  • active compound or active compound combination 1 part by weight of active compound or active compound combination is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration, or a commercial formulation of active compound or active compound combination is diluted with water to the desired concentration.
  • the activity found for the active compound combination according to the invention is greater than the calculated activity, i.e. there is a synergistic effect.
  • the combination of the compound of the formula (1) and the halogeno-benzimidazole of the formula No. XXVII has an actual efficacy of 73%.
  • the expected value, calculated using Colby's formula is considerably lower.

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  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
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Abstract

The present invention relates to fungicidally active compound combinations of a fluorobenzothiazole derivative of the formula (I)
Figure US07208510-20070424-C00001
and at least one of the compounds listed in the disclosure.

Description

RELATED APPLICATIONS
This application is a division of U.S. application Ser. No. 10/619,730, filed Jul. 15, 2003, which is a division of U.S. application Ser. No. 10/149,353, filed Jun. 7, 2002, now U.S. Pat. No. 6,624,183, issued Sep. 23, 2003, which was filed under 35 U.S.C. 371 as a national stage application of International Application No. PCT/EP00/11989, filed Nov. 30, 2000, which was published in German as International Patent Publication WO 01/44215 on Jun. 21, 2001, which is entitled to the right of priority of German Patent Applications 199 59 947.5, filed Dec. 13, 1999, and 100 21 412.6, filed May 3, 2000.
The present invention relates to novel active compound combinations which consist of a known fluoro-benzothiazole derivative and further known fungicidally active compounds, and which are highly suitable for controlling phytopathogenic fungi.
It is already known that isopropyl 1-({[1-(6-fluoro-1,3-benzothiazol-2-yl)ethyl]-amino}carbonyl)-2-methylpropylcarbamate has fungicidal properties (cf. EP-A1-775 696). The activity of this compound is good; however, at low application rates it is in some cases not satisfactory.
Furthermore, it is already known that a large number of triazole derivatives, aniline derivatives, dicarboximides and other heterocycles can be employed for controlling fungi (cf. EP-A 0 040 345, DE-A 22 01 063, DE-A 23 24 010, Pesticide Manual, 9th Edition (1991), pages 249 and 827, EP-A 0 382 375 and EP-A 0 515 901). Likewise, the activity of these compounds is not always satisfactory at low application rates.
Finally, it is also known that 1-[(6-chloro-3-pyridinyl)-methyl]-N-nitro-2-imidazolidineimine can be used for controlling animal pests such as insects (cf. Pesticide Manual, 9th Edition (1991), page 491). However, fungicidal properties have hitherto not been described for this compound.
Furthermore, it is already known that 1-(3,5-dimethyl-isoxazol-4-sulphonyl)-2-chloro-6,6-difluoro-[1,3]-dioxolo-[4,5f]-benzimidazole has fungicidal properties (cf. WO 97-06171).
Furthermore, it is already known that substituted azodioxacycloalkenes have fungicidal properties (cf. EP-B-712 396).
Finally, it is also known that substituted halogenopyrimidines have fungicidal properties (cf. DE-A1-196 46 407, EP-B-712 396).
It has now been found that the novel active compound combinations comprising a fluorobenzothiazole derivative of the formula
Figure US07208510-20070424-C00002
and
  • (1) a triazole derivative of the formula
Figure US07208510-20070424-C00003
    • in which
    • X represents chlorine or phenyl and
    • Y represents
Figure US07208510-20070424-C00004
and/or
  • (2) the triazole derivative of the formula
Figure US07208510-20070424-C00005
and/or
  • (3) an aniline derivative of the formula
Figure US07208510-20070424-C00006
    • in which
    • R1 represents hydrogen or methyl,
      and/or
  • (4) N-[1-(4-chloro-phenyl)-ethyl]-2,2-dichloro-1-ethyl-3-methyl-cyclopropane-carboxamide of the formula
Figure US07208510-20070424-C00007
and/or
  • (5) the zinc propylene-1,2-bis-(dithiocarbamidate) of the formula
Figure US07208510-20070424-C00008
and/or
  • (6) at least one thiocarbamate of the formula
Figure US07208510-20070424-C00009
    • Me=Zn or Mn or a mixture of Zn and Mn
      and/or
  • (7) the aniline derivative of the formula
Figure US07208510-20070424-C00010
and/or
  • (8) the compound of the formula
Figure US07208510-20070424-C00011
and/or
  • (9) the benzothiadiazole derivative of the formula
Figure US07208510-20070424-C00012
and/or
  • (10) the 8-t-butyl-2-(N-ethyl-N-n-propyl-amino)-methyl-1,4-dioxaspiro[5,4]-decane of the formula
Figure US07208510-20070424-C00013
and/or
  • (11) the compound of the formula
Figure US07208510-20070424-C00014
and/or
  • (12) the compound of the formula
Figure US07208510-20070424-C00015
and/or
  • (13) the compound of the formula
Figure US07208510-20070424-C00016
and/or
  • (14) the cyanoxime derivative of the formula
Figure US07208510-20070424-C00017
and/or
  • (15) a pyrimidine derivative of the formula
Figure US07208510-20070424-C00018
    • in which
    • R2 represents methyl, —C≡C—CH3 (mepanipyrim) or cyclopropyl (cyprodinyl),
      and/or
  • (16) an aniline derivative of the formula
Figure US07208510-20070424-C00019
and/or
  • (17) the morpholine derivative of the formula
Figure US07208510-20070424-C00020
and/or
  • (18) the phthalimide derivative of the formula
Figure US07208510-20070424-C00021
and/or
  • (19) the phosphorus compound of the formula
Figure US07208510-20070424-C00022
and/or
  • (20) the hydroxyethyl-triazole derivative of the formula
Figure US07208510-20070424-C00023
and/or
  • (21) the 1-[(6-chloro-3-pyridinyl)-methyl]-N-nitro-2-imidazolidinimine of the formula
Figure US07208510-20070424-C00024
and/or
  • (22) the oxazolidinedione of the formula
Figure US07208510-20070424-C00025
and/or
  • (23) the benzamide derivative of the formula
Figure US07208510-20070424-C00026
and/or
  • (24) a guanidine derivative of the formula
Figure US07208510-20070424-C00027
    • in which
    • m represents integers from 0 to 5 and
    • R3 represents hydrogen (17 to 23%) or the radical of the formula
Figure US07208510-20070424-C00028
and/or
  • (25) the triazole derivative of the formula
Figure US07208510-20070424-C00029
and/or
  • (26) the halogeno-benzimidazole of the formula
Figure US07208510-20070424-C00030
and/or
  • (27) the halogenopyrimidine of the formula
Figure US07208510-20070424-C00031
and/or
  • (28) the tetrachloro-isophthalo-dinitrile of the formula
Figure US07208510-20070424-C00032
and/or
  • (29) the compound of the formula
Figure US07208510-20070424-C00033
and/or
  • (30) the pyridineamine of the formula
Figure US07208510-20070424-C00034
and/or
  • (31) the thiazolecarboxamide of the formula
Figure US07208510-20070424-C00035
and/or
  • (32) the sulphonamide of the formula
Figure US07208510-20070424-C00036
and/or
  • (33) the compound of the formula
Figure US07208510-20070424-C00037
and/or
  • (34) the compound of the formula
Figure US07208510-20070424-C00038
and/or
  • (35) the compound of the formula
Figure US07208510-20070424-C00039
and/or
  • (36) the diamide of the formula
Figure US07208510-20070424-C00040
and/or
  • (37) the methoxyacrylate derivative of the formula
Figure US07208510-20070424-C00041
and/or
  • (38) the quinoline derivative of the formula
Figure US07208510-20070424-C00042
and/or
  • (39) the phenylamide derivative of the formula
Figure US07208510-20070424-C00043
and/or
  • (40) the phenylamide derivative of the formula
Figure US07208510-20070424-C00044
and/or
  • (41) the dicarboxime derivative of the formula
Figure US07208510-20070424-C00045
and/or
  • (42) the phosphonic acid of the formula
Figure US07208510-20070424-C00046
and/or
  • (43) the pyrrole derivative of the formula
Figure US07208510-20070424-C00047
and/or
  • (44) the phenyl carbonate of the formula
Figure US07208510-20070424-C00048
and/or
  • (45) the copper compounds
  • a) copper oxychloride (XXXXVIa)
  • b) copper hydroxid (XXXXVIb)
    and/or
  • (46) the imidazole derivative of the formula
Figure US07208510-20070424-C00049
and/or
  • (47) the triazole derivative of the formula
  • a)
Figure US07208510-20070424-C00050
and/or
  • b)
Figure US07208510-20070424-C00051
and/or
  • c)
Figure US07208510-20070424-C00052
and/or
  • d)
Figure US07208510-20070424-C00053
and/or
  • e)
Figure US07208510-20070424-C00054
and/or
  • f)
Figure US07208510-20070424-C00055
and/or
  • g)
Figure US07208510-20070424-C00056
and/or
  • h)
Figure US07208510-20070424-C00057
and/or
  • (48) a compound of the general formula
Figure US07208510-20070424-C00058
    • in which
    • R1 represents unsubstituted or fluorine-, chlorine-, bromine-, methyl- or ethyl-substituted phenyl, 2-naphthyl, 1,2,3,4-tetrahydronaphthyl or indanyl,
      and/or
  • (49) N-methyl-2-(methoxyimino)-2-[2-([1-(3-tri-fluoro-methyl-phenyl)ethoxy]iminomethyl)phenyl]acetamide of the formula
Figure US07208510-20070424-C00059
and/or
  • (50) 2,4-dihydro-5-methoxy-2-methyl-4-[2-([([1-(3-tri-fluoro-methylphenyl)ethylidene]amino)oxy]methyl)phenyl]-3H-1,2,4-triazol-3-one of the formula
Figure US07208510-20070424-C00060
and/or
  • (51) the compound of the formula
Figure US07208510-20070424-C00061
have very good fungicidal properties.
Surprisingly, the fungicidal activity of the active compound combinations according to the invention is considerably higher than the sum of the activities of the individual active compounds. Thus, an unforeseeable, true synergistic effect is present, and not just an addition of activities.
From the structural formula of the active compound of the formula (I), it can be seen that the compound has two asymmetrically substituted carbon atoms. Accordingly, the product can be present as a mixture of different isomers or else in the form of a single isomer.
Preferred compounds of the formula (I) are compounds in which the amino acid moiety is formed from i-propyloxycarbonyl-L-valine and the fluoro-benzothiazoleethylamine moiety is racemic, but has, in particular, the (R) configuration.
The formula (II) includes the compounds
  • 1-(4-chloro-phenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-butan-2-one of the formula
Figure US07208510-20070424-C00062
  • 1-(4-chloro-phenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-butan-2-ol of the formula
Figure US07208510-20070424-C00063
and
  • 1-(4-phenyl-phenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-butan-2-ol of the formula
Figure US07208510-20070424-C00064
The formula (IV) includes the aniline derivatives of the formulae
Figure US07208510-20070424-C00065
and
Figure US07208510-20070424-C00066
It is evident from the structural formula for the active compound of the formula (V) that the compound has three asymmetrically substituted carbon atoms. The product may therefore be present as a mixture of different isomers, or else in the form of a single component. Particular preference is given to the compounds
  • N-(R)-[1-(4-chloro-phenyl)-ethyl]-(1S)-2,2-dichloro-1-ethyl-3t-methyl-1R-cyclopropanecarboxamide of the formula
Figure US07208510-20070424-C00067
and
  • N-(R)-[1-(4-chloro-phenyl)-ethyl]-(1R)-2,2-dichloro-1-ethyl-3t-methyl-1R-cyclopropanecarboxamide of the formula
Figure US07208510-20070424-C00068
The formula (VII) includes the compounds
(VIIa) Me=Zn (zineb),
(VIIb) Me=Mn (maneb) and
(VIIc) mixture of (VIIa) and (VIIb) (mancozeb).
The formula (XVI) includes the compounds
Figure US07208510-20070424-C00069
The compound of the formula (XVII) can be present as methyl N-(2,6-dimethylphenyl)-N-(methoxyacetyl)-DL-alaninate (metalaxyl, XVIIa) or as methyl N-(2,6-dimethylphenyl)-N-(methoxyacetyl)-D-alaninate (metalaxyl-M, XVIIb).
The hydroxyethyl-triazole derivative of the formula (XXI) can be present in the “thiono” form of the formula
Figure US07208510-20070424-C00070
or in the tautomeric “mercapto” form of the formula
Figure US07208510-20070424-C00071
For simplicity's sake, only the “thiono” form is given in each case.
The guanidine derivative of the formula (XXV) is a substance mixture with the common name guazatine.
From the structural formula for the active compouds of the formula (XXXXIX), it can be seen that the compounds can be present as E or Z isomers. Accordingly, the product can be present as a mixture of different isomers or else in the form of a single isomer. Preference is given to compounds of the formula (XXXXIX) in which the compounds of the formula (XXXXIX) are present as E isomer. Particular preference is given to the compounds of the formulae
Figure US07208510-20070424-C00072
and their isomers.
The following active compounds are particularly preferred mixing partners of the compounds of the formula (I):
  • (3) tolylfluanid (IVb),
  • (5) propineb (VI),
  • (6) mancozeb (VIIc),
  • (7) fenhexamid (VIII),
  • (8) iprovalicarb (VIII),
  • (11) azoxystrobin (XII),
  • (12) trifloxystrobin (XIII),
  • (13) compound of the formula (XIV),
  • (18) folpet (XIX),
  • (20) compound of the formula (XXI),
  • (26) compound of the formula (XXVII),
  • (27) compound of the formula (XXVIII),
  • (28) chlorothalonil (XXIX),
  • (30) fluazinam (XXXI), and
  • (45) copper compounds
    • a) copper oxychloride (XXXXVIa)
    • b) copper hydroxide (XXXXVIb).
The components which are present in the active combinations according to the invention in addition to a halogeno-benzimidazole of the formula (XXVII) are also known.
Specifically, the active compounds are described in the following publications:
  • (1) compounds of the formula (H)
    • DE-A 22 01 063
    • DE-A 23 24 010
  • (2) compound of the formula (III)
    • EP-A 0 040 345
  • (3) compounds of the formula (IV)
    • Pesticide Manual, 9th Ed. (1991), pages 249 and 827
  • (4) compound of the formula (V) and individual derivatives thereof.
    • EP-A 0 341 475
  • (5) compound of the formula (VI)
    • Pesticide Manual, 9th Ed. (1991), page 726
  • (6) compounds of the formula (VII)
    • Pesticide Manual, 9th Ed. (1991), pages 529, 531 and 866
  • (7) compound of the formula (VIII)
    • EP-A 0 339 418
  • (8) compound of the formula (IX)
    • EP-A 0 472 996
  • (9) compound of the formula (X)
    • EP-A 0 313 512
  • (10) compound of the formula (XI)
    • EP-A 0 281 842
  • (11) compound of the formula (XII)
    • EP-A 0 382 375
  • (12) compound of the formula (XIII)
    • EP-A460 575
  • (13) compound of the formula (XIV)
    • DE-A 196 02 095
  • (14) compound of the formula (XV)
    • Pesticide Manual, 9th Ed. (1991), page 206
  • (15) compounds of the formula (XVI)
    • EP-A 0 270 111
    • EP-A 0 310 550
  • (16) compound of the formula (XVII)
    • Pesticide Manual, 9th Ed. (1991), page 554
  • (17) compound of the formula (XVIII)
    • EP-A0219 756
  • (18) compound of the formula (XIX)
    • Pesticide Manual, 9th Ed. (1991), page 431
  • (19) compound of the formula (XX)
    • Pesticide Manual, 9th Ed. (1991), page 443
  • (20) compound of the formula (XXI)
    • WO 96-16048
  • (21) compound of the formula (XXII)
    • Pesticide Manual, 9th Ed. (1991), page 491
  • (22) compound of the formula (XXII)
    • EP-A 0 393 911
  • (23) compound of the formula (XXIV)
    • EP-A 0 600 629
  • (24) substance of the formula (XXV)
    • Pesticide Manual, 9th Ed. (1991), page 461
  • (25) compound of the formula (XXVI)
    • Pesticide Manual, 9th Ed. (1991), page 654
  • (26) compound of the formula (XXVII)
    • WO 97-06171
  • (27) compound of the formula (XXVIII)
    • DE-A1-196 46 407, EP-B-0 712 396
  • (28) compound of the formula (XXIX)
    • U.S. Pat. No. 3,290,353
  • (29) compound of the formula (XXX)
    • DE-A-156 7169
  • (30) compound of the formula (XXXI)
    • EP-A-0 031 257
  • (31) compound of the formula (XXXII)
    • EP-A-0 639 547
  • (32) compound of the formula (XXXI)
    • EP-A-0 298 196
  • (33) compound of the formula (XXXIV)
    • EP-A-600 629
  • (34) compound of the formula (XXXV)
    • DE-A-2 149 923
  • (35) compound of the formula (XXXVI)
    • DE-A-2 012 656
  • (36) compound of the formula (XXXVII)
    • U.S. Pat. No. 1,972,961
  • (37) compound of the formula (XXXVIII)
    • EP-A-326 330
  • (38) compound of the formula (XXXI)
    • EP-A 278 595
  • (39) compound of the formula (XXXX)
    • DE-A-3 030 026
  • (40) compound of the formula (XXXXI)
    • DE-A-2 903 612
  • (41) compound of the formula (XXXXII)
    • U.S. Pat. No. 2,553,770
  • (42) compound of the formula (XXXXIII)
    • known and commercially available
  • (43) compound of the formula (XXXXIV)
    • EP-A-206 999
  • (44) compound of the formula (XXXXV)
    • EP-A-78 663
  • (45) a) compound of the formula (XXXXVIa)
    • known and commercially available
  •  b) compound of the formula (XXXXVIb)
    • known and commercially available
  • (46) compound of the formula (XXXXVII)
    • DE-A-2 429 523
  • (47) a) compound of the formula (XXXXVIa)
    • EP-A-112 284
  •  b) compound of the formula (XXXXVIIIb)
    • DE-A-3 042 303
  •  c) compound of the formula (XXXXVIIIc)
    • DE-A-3 406 993
  •  d) compound of the formula (XXXXVIIId)
    • EP-A-68 813
  •  e) compound of the formula (XXXXVIIIe)
    • DE-A-2551560
  •  f) compound of the formula (XXXXVIIIf)
    • EP-A-145 294
  •  g) compound of the formula (XXXXVIIIg)
    • DE-A-3 721 786
  •  h) compound of the formula (XXXXVIIIh)
    • EP-A-234 242
  • (48) compound of the formula (XXXXIX)
    • WO 96/23763
  • (49) compound of the formula (XXXXX)
    • EP-A-596 254
  • (50) compound of the formula (XXXXXI)
    • WO 98/23155
  • (50) compound of the formula (XXXXXII)
    • EP-A-569 384.
In addition to an active compound of the formula (I), the active compound combinations according to the invention comprise at least one active compound of the compounds of groups (1) to (51). Additionally, they may comprise further fungicidally active additives.
The synergistic effect is particularly pronounced when the active compounds in the active compound combinations according to the invention are present in certain weight ratios. However, the weight ratios of the active compounds in the active compound combinations can be varied within a relatively wide range. In general,
from 0.1 to 50 parts by weight, preferably from 0.2 to 20 parts by weight, of active compound of group (1),
from 0.1 to 50 parts by weight, preferably from 0.2 to 20 parts by weight, of active compound of group (2),
from 1 to 150 parts by weight, preferably from 1 to 100 parts by weight, of active compound of group (3),
from 0.1 to 10 parts by weight, preferably from 0.2 to 5 parts by weight, of active compound of group (4),
from 1 to 150 parts by weight, preferably from 5 to 100 parts by weight, of active compound of group (5),
from 1 to 150 parts by weight, preferably from 5 to 100 parts by weight, of active compound of group (6),
from 0.1 to 50 parts by weight, preferably from 1 to 20 parts by weight, of active compound of group (7),
from 0.1 to 50 parts by weight, preferably from 0.2 to 20 parts by weight, of active compound of group (8),
from 0.02 to 50 parts by weight, preferably from 0.1 to 10 parts by weight, of active compound of group (9),
from 0.1 to 50 parts by weight, preferably from 0.2 to 20 parts by weight, of active compound of group (10),
from 0.1 to 50 parts by weight, preferably from 0.2 to 20 parts by weight, of active compound of group (11),
from 0.1 to 50 parts by weight, preferably from 0.2 to 20 parts by weight, of active compound of group (12),
from 0.1 to 50 parts by weight, preferably from 0.2 to 20 parts by weight, of active compound of group (13),
from 0.1 to 50 parts by weight, preferably from 0.2 to 20 parts by weight, of active compound of group (14),
from 0.2 to 50 parts by weight, preferably from 1 to 20 parts by weight, of active compound of group (15),
from 0.1 to 50 parts by weight, preferably from 0.2 to 20 parts by weight, of active compound of group (16),
from 0.1 to 50 parts by weight, preferably from 0.2 to 20 parts by weight, of active compound of group (17),
from 1 to 150 parts by weight, preferably from 5 to 100 parts by weight, of active compound of group (18),
from 0.1 to 150 parts by weight, preferably from 1 to 100 parts by weight, of active compound of group (19),
from 0.02 to 50 parts by weight, preferably from 0.2 to 10 parts by weight, of active compound of group (20),
from 0.05 to 20 parts by weight, preferably from 0.1 to 10 parts by weight, of active compound of group (21),
from 0.1 to 50 parts by weight, preferably from 0.2 to 20 parts by weight, of active compound of group (22),
from 0.1 to 50 parts by weight, preferably from 0.2 to 20 parts by weight, of active compound of group (23),
from 0.01 to 150 parts by weight, preferably from 1 to 100 parts by weight, of active compound of group (24),
from 0.1 to 50 parts by weight, preferably from 0.2 to 20 parts by weight, of active compound of group (25),
from 0.1 to 50 parts by weight, preferably from 0.2 to 20 parts by weight, of active compound of group (26),
from 0.1 to 50 parts by weight, preferably from 0.2 to 20 parts by weight, of active compound of group (27),
from 1 to 150 parts by weight, preferably from 5 to 100 parts by weight, of active compound of group (28),
from 1 to 150 parts by weight, preferably from 5 to 100 parts by weight, of active compound of group (29),
from 0.1 to 50 parts by weight, preferably from 0.2 to 20 parts by weight, of active compound of group (30),
from 0.1 to 50 parts by weight, preferably from 0.2 to 20 parts by weight, of active compound of group (31),
from 0.1 to 50 parts by weight, preferably from 0.2 to 20 parts by weight, of active compound of group (32),
from 0.1 to 50 parts by weight, preferably from 0.2 to 20 parts by weight, of active compound of group (33),
from 0.1 to 50 parts by weight, preferably 1 to 20 parts by weight, of active compound of group (34),
from 0.1 to 50 parts by weight, preferably from 1 to 10 parts by weight, of active compound of group (35),
from 1 to 150 parts by weight, preferably from 5 to 100 parts by weight, of active compound of group (36),
from 0.1 to 50 parts by weight, preferably from 0.2 to 20 parts by weight, of active compound of group (37).
from 0.1 to 50 parts by weight, preferably from 0.2 to 20 parts by weight, of active compound of group (38),
from 0.1 to 50 parts by weight, preferably from 0.2 to 20 parts by weight, of active compound of group (39),
from 0.1 to 50 parts by weight, preferably from 0.2 to 20 parts by weight, of active compound of group (40),
from 1 to 150 parts by weight, preferably from 5 to 100 parts by weight, of active compound of group (41),
from 1 to 150 parts by weight, preferably from 5 to 100 parts by weight, of active compound of group (42),
from 0.1 to 50 parts by weight, preferably from 1 to 20 parts by weight, of active compound of group (43),
from 0.1 to 50 parts by weight, preferably from 1 to 20 parts by weight, of active compound of group (44),
from 1 to 150 parts by weight, preferably from 5 to 100 parts by weight, of active compound of group (45a),
from 1 to 150 parts by weight, preferably from 5 to 100 parts by weight, of active compound of group (45b),
from 0.1 to 50 parts by weight, preferably from 0.2 to 20 parts by weight, of active compound of group (46),
from 0.1 to 50 parts by weight, preferably from 0.2 to 20 parts by weight, of active compound of group (47a),
from 0.1 to 50 parts by weight, preferably from 0.2 to 20 parts by weight, of active compound of group (47b),
from 0.1 to 50 parts by weight, preferably from 0.2 to 20 parts by weight, of active compound of group (47c),
from 0.1 to 50 parts by weight, preferably from 0.2 to 20 parts by weight, of active compound of group (47d),
from 0.1 to 50 parts by weight, preferably from 0.2 to 20 parts by weight, of active compound of group (47e),
from 0.1 to 50 parts by weight, preferably from 0.2 to 20 parts by weight, of active compound of group (47f),
from 0.1 to 50 parts by weight, preferably 0.2 to 20 parts by weight, of active compound of group (47g),
from 0.1 to 50 parts by weight, preferably from 0.2 to 20 parts by weight, of active compound of group (47h),
from 0.1 to 50 parts by weight, preferably 0.2 to 20 parts by weight, of active compound of group (48),
from 0.1 to 50 parts by weight, preferably from 0.2 to 20 parts by weight, of active compound of group (49),
from 0.1 to 50 parts by weight, preferably from 0.2 to 20 parts by weight, of active compound of group (50),
from 0.1 to 50 parts by weight, preferably from 0.2 to 20 parts by weight, of active compound of group (51)
are present per part by weight of active compound of the formula (I).
The active compound combinations according to the invention have very good fungicidal properties and can be employed for controlling phytopathogenic fungi, such as Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes, Deuteromycetes, etc.
The active compound combinations according to the invention are particularly suitable for controlling Phytophthora infestans and Plasmopara viticola.
The fact that the active compound combinations are well tolerated by plants at the concentrations required for controlling plant diseases permits the treatment of above-ground parts of plants, of propagation stock and seeds, and of the soil. The active compound combinations according to the invention can be employed for foliar application or else as seed dressings.
The active compound combinations according to the invention may also be employed to increase the yield of crops. However, they have reduced toxicity and are tolerated well by plants.
According to the invention, it is possible to treat all plants and parts of plants. Plants are to be understood here as meaning all plants and plant populations such as desired and undesired wild plants or crop plants (including naturally occurring crop plants). Crop plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including plant cultivars which can or cannot be protected by plant breeders certificates. Parts of plants are to be understood as meaning all above-ground and below-ground parts and organs of plants, such as shoot, leaf, flower and root, examples which may be mentioned being leaves, needles, stems, trunks, flowers, fruit-bodies, fruits and seeds and also roots, tubers and rhizomes. Parts of plants also include harvested plants and vegetative and generative propagation material, for example seedlings, tubers, rhizomes, cuttings and seeds.
The treatment of the plants and parts of plants according to the invention with the active compounds is carried out directly or by action on their environment, habitat or storage area according to customary treatment methods, for example by dipping, spraying, evaporating, atomizing, broadcasting, brushing-on and, in the case of propagation material, in particular in the case of seeds, furthermore by one- or multi-layer coating.
The active compound combinations according to the invention can be converted to the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols and microencapsulations in polymeric substances and in coating compositions for seeds, and ULV formulations.
These formulations are produced in a known manner, for example by mixing the active compounds or active compound combinations with extenders, that is liquid solvents, liquefied gases under pressure, and/or solid carriers, optionally with the use of surfactants, that is emulsifiers and/or dispersants, and/or foam formers. If the extender used is water, it is also possible to use, for example, organic solvents as auxiliary solvents. Essentially, suitable liquid solvents include: aromatics such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, for example petroleum fractions, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulphoxide, or else water. Liquefied gaseous extenders or carriers are to be understood as meaning liquids which are gaseous at ambient temperature and under atmospheric pressure, for example aerosol propellants such as butane, propane, nitrogen and carbon dioxide. Suitable solid carriers are: for example ground natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals such as finely divided silica, alumina and silicates. Suitable solid carriers for granules are: for example crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, or else synthetic granules of inorganic and organic meals, and granules of organic material such as sawdust, coconut shells, maize cobs and tobacco stalks. Suitable emulsifiers and/or foam formers are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonates, or else protein hydrolysates. Suitable dispersants are: for example lignin-sulphite waste liquors and methylcellulose.
Tackifiers such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, or else natural phospholipids such as cephalins and lecithins and synthetic phospholipids can be used in the formulations. Other additives can be mineral and vegetable oils.
It is possible to use colorants such as inorganic pigments, for example iron oxide, titanium oxide and Prussian Blue, and organic dyestuffs such as alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
The formulations generally comprise between 0.1 and 95% by weight of active compounds, preferably between 0.5 and 90%.
The active compound combinations according to the invention, as such or in their formulations, can also be applied in a mixture with known fungicides, bactericides, acaricides, nematicides or insecticides, to broaden the activity spectrum or to prevent the development of resistance, for example. In many cases, synergistic effects are obtained, i.e. the activity of the mixture is greater than the activity of the individual components.
A mixture with other known active compounds such as herbicides or with fertilizers and growth regulators is also possible.
The active compound combinations can be used as such, in the form of their formulations or as the use forms prepared therefrom, such as ready-to-use solutions, emulsifiable concentrates, emulsions, suspensions, wettable powders, soluble powders and granules. They are used in the customary manner, for example by watering, spraying, atomizing, scattering, spreading, and as a powder for dry seed treatment, a solution for seed treatment, a water-soluble powder for seed treatment, a water-soluble powder for slurry treatment, or by encrusting.
When using the active compound combinations according to the invention, the application rates can be varied within a relatively wide range, depending on the kind of application. In the treatment of parts of plants, the application rates of the active compound combination are generally between 0.1 and 10,000 g/ha, preferably between 10 and 1000 g/ha. In the treatment of seeds, the application rates of the active compound combination are generally between 0.001 and 50 g per kilogram of seed, preferably between 0.01 and 10 g per kilogram of seed. In the treatment of the soil, the application rates of the active compound combination are generally between 0.1 and 10,000 g/ha, preferably between 1 and 5000 g/ha.
The good fungicidal activity of the active compound combinations according to the invention is evident from the examples below. While the individual active compounds exhibit weaknesses with regard to the fungicidal activity, the combinations have an activity which exceeds the sum of individual activities.
A synergistic effect of fungicides is always present when the fungicidal activity of the active compound combinations exceeds the total of the activities of the active compounds when applied individually.
The expected activity for a given combination of two active compounds can be calculated as follows (cf. Colby, S. R., “Calculating Synergistic and Antagonistic Responses of Herbicide Combinations”, Weeds 15, (1967), 20-22):
If
X is the efficacy when applying active compound A at an application rate of m g/ha,
Y is the efficacy when applying active compound B at an application rate of n g/ha and
E is the efficacy when applying the active compounds A and B at an application rate of m and n g/ha,
    • then
E = X + Y - X · Y 100
The efficacy is calculated in %. 0% is an efficacy which corresponds to that of the control, whereas an efficacy of 100% means that no infection is observed.
If the actual fungicidal activity exceeds the calculated value, then the activity of the combination is superadditive, i.e. a synergistic effect exists. In this case, the efficacy which was actually observed must be greater than the value for the expected efficacy (E) calculated from the abovementioned formula.
The examples that follow illustrate the invention. However, the invention is not limited to the examples.
EXAMPLE 1
Phytophthora Test (Tomato)/Protective
Solvent: 47 parts by weight of acetone
Emulsifier:  3 parts by weight of alkylaryl polyglycol ether
To produce a suitable preparation of active compound, 1 part by weight of active compound or active compound combination is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration, or a commercial formulation of active compound or active compound combination is diluted with water to the desired concentration.
To test for protective activity, young plants are sprayed with the active compound preparation at the stated application rate. After the spray coating has dried on, the plants are inoculated with an aqueous spore suspension of Phytophthora infestans. The plants are then placed in an incubation cabin at about 20° C. and 100% relative atmospheric humidity.
Evaluation is carried out 3 days after the inoculation. 0% means an efficacy which corresponds to that of the control, whereas an efficacy of 100% means that no infection is observed.
The activity found for the active compound combination according to the invention is greater than the calculated activity, i.e. there is a synergistic effect. At a mixing ratio of 1:1 and an application rate of 0.1 g/ha, the combination of the compound of the formula (1) and the halogeno-benzimidazole of the formula No. XXVII has an actual efficacy of 73%. At 63%, the expected value, calculated using Colby's formula, is considerably lower.
Active compounds, application rates and test results are shown in the tables below.
TABLE 1
Phytophthora test (tomato)/protective
Active
compound Effi-
Active compound application cacy
known: rate in g/ha in %
compound of the formula (XXVII) 0.1 30
Figure US07208510-20070424-C00073
compound of the formula (I) 0.1 47
Figure US07208510-20070424-C00074
Mixture according to the invention:
Active
compound Expected value,
Mixing application Actual calculated using
Active compound ratio rate in g/ha efficacy Colby's formula
XXVII 0.1 63
+ {close oversize brace} 1:1 + {close oversize brace} 73
I 0.1
TABLE 2
Phytophthora test (tomato)/protective
Active
compound Effi-
Active compound application cacy
known: rate in g/ha in %
compound of the formula (I)  1 47
Figure US07208510-20070424-C00075
propineb (VI) 20 19
(VI)
Figure US07208510-20070424-C00076
Mixture according to the invention
Active
compound Expected value
application Actual calculated using
Mixing ratio rate in g/ha efficacy Colby's formula
(I) 1 57
+ {close oversize brace} 1:20 + {close oversize brace} 94
propineb (VI) 20
TABLE 3
Phytophthora test (tomato)/protective
Active
compound Effi-
Active compound application cacy
known: rate in g/ha in %
compound of the formula (I)  1 47
Figure US07208510-20070424-C00077
chlorothalonil (XXIX) 20 12
Figure US07208510-20070424-C00078
Mixture according to the invention
Active
compound Expected value
application Actual calculated using
Mixing ratio rate in g/ha efficacy Colby's formula
(I) 1 53
+ + {close oversize brace} 84
chlorothalonil {close oversize brace} 1:20 20
(XXIX)
TABLE 4
Phytophthora test (tomato)/protective
Active
compound Effi-
Active compound application cacy
known: rate in g/ha in %
compound of the formula (I)  1 47
Figure US07208510-20070424-C00079
dichlofluanid (IVa) 20  5
Figure US07208510-20070424-C00080
Mixture according to the invention:
Active
compound Expected value
application Actual calculated using
Mixing ratio rate in g/ha efficacy Colby's formula
(I) 1 50
+ + {close oversize brace} 87
dichlofluanid {close oversize brace} 1:20 20
(IVa)
TABLE 5
Phytophthora test (tomato)/protective
Active
compound Effi-
Active compound application cacy
known: rate in g/ha in %
compound of the formula (I)  1 47
Figure US07208510-20070424-C00081
tolylfluanid (IVb) 20 21
Figure US07208510-20070424-C00082
Mixture according to the invention:
Active Expected
compound value
application Actual calculated using
Mixing ratio rate in g/ha efficacy Colby's formula
(I) 1 58
+ + {close oversize brace} 95
tolyifluanid {close oversize brace} 1:20 20
(IVa)
TABLE 6
Phytophthora test (tomato)/protective
Active
compound Effi-
Active compound application cacy
known: rate in g/ha in %
compound of the formula (I)  1 47
Figure US07208510-20070424-C00083
folpet (XIX) 20  0
Figure US07208510-20070424-C00084
Mixture according to the invention:
Active Expected
compound value
application Actual calculated using
Mixing ratio rate in g/ha efficacy Colby's formula
(I) 1 47
+ {close oversize brace} 1:20 + {close oversize brace} 95
folpet (XIX) 20
TABLE 7
Phytophthora test tomato/protective
Active
compound Effi-
Active compound application cacy
known: rate in g/ha in %
compound of the formula (I)  1 39
Figure US07208510-20070424-C00085
mancozeb (VIIc) 20 28
Mixture according to the invention:
Expected
Active value calcu-
compound lated using
application Actual Colby's
Mixing ratio rate in g/ha efficacy formula
(I) 1 56
+ {close oversize brace} 1:20 + {close oversize brace} 68
mancozeb (VIIc) 20
TABLE 8
Phytophthora test (tomato)/protective
Active
compound Effi-
Active compound application cacy
known: rate in g/ha in %
compound of the formula (I)  1 47
Figure US07208510-20070424-C00086
bitertanol (IIc) 10  4
Mixture according to the invention:
Active
compound Expected value
application Actual calculated using
Mixing ratio rate in g/ha efficacy Colby's formula
(I) 1 49
+ {close oversize brace} 1:10 + {close oversize brace} 73
bitertanol (IIc) 10
TABLE 9
Phytophthora test (tomato)/protective
Active
compound Effi-
Active compound application cacy
known: rate in g/ha in %
compound of the formula (I)  1 47
Figure US07208510-20070424-C00087
tebuconazole (III) 10  5
Figure US07208510-20070424-C00088
Mixture according to the invention:
Active
compound Expected value
application Actual calculated using
Mixing ratio rate in g/ha efficacy Colby's formula
(I) 1 50
+ + {close oversize brace} 73
tebuconazole {close oversize brace} 1:10 10
(III)
TABLE 10
Phytophthora test (tomato)/protective
Active
compound Effi-
Active compound application cacy
known: rate in g/ha in %
compound of the formula (I)  1 47
Figure US07208510-20070424-C00089
triadimenol (IIb) 10  0
Mixture according to the invention:
Active
compound Expected value
application Actual calculated using
Mixing ratio rate in g/ha efficacy Colby's formula
(I) 1 47
+ + {close oversize brace} 88
triadimenol {close oversize brace} 1:10 10
(IIb)
TABLE 11
Phytophthora test (tomato)/protective
Active
compound Effi-
Active compound application cacy
known: rate in g/ha in %
compound of the formula (I)  1 47
Figure US07208510-20070424-C00090
imidacloprid (XXII) 10  0
Figure US07208510-20070424-C00091
Mixture according to the invention:
Active
compound Expected value
application Actual calculated using
Mixing ratio rate in g/ha efficacy Colby's formula
(I) 1 47
+ + {close oversize brace} 71
imidacloprid {close oversize brace} 1:10 10
(XXII)
TABLE 12
Phytophthora test (tomato)/protective
Active
compound Effi-
Active compound application cacy
known: rate in g/ha in %
compound of the formula (I)  1 47
Figure US07208510-20070424-C00092
compound of the formula (XXI) (20) 10  2
(XXI)
Figure US07208510-20070424-C00093
Mixture according to the invention:
Active
compound Expected value
application Actual calculated using
Mixing ratio rate in g/ha efficacy Colby's formula
(I) 1 48
+ {close oversize brace} 1:10 + {close oversize brace} 62
(XXI) (20) 10
TABLE 13
Phytophthora test (tomato)/protective
Active
compound Effi-
Active compound application cacy
known: rate in g/ha in %
compound of the formula (I)  1 47
Figure US07208510-20070424-C00094
fenhexamid (VIII) 10 13
Figure US07208510-20070424-C00095
Mixture according to the invention:
Active
compound Expected value
application Actual calculated using
Mixing ratio rate in g/ha efficacy Colby's formula
(I) 1 54
+ + {close oversize brace} 70
fenhexamid {close oversize brace} 1:10 10
(VIII)
TABLE 14
Phytophthora test (tomato)/protective
Active
compound Effi-
Active compound application cacy
known: rate in g/ha in %
compound of the formula (I)  1 47
Figure US07208510-20070424-C00096
carpropamid (V) 10  0
Figure US07208510-20070424-C00097
Mixture according to the invention:
Active Expected value
compound calculated
application Actual using Colby's
Mixing ratio rate in g/ha efficacy formula
(I) 1 47
+ {close oversize brace} 1:10 + {close oversize brace} 90
carpropamid (V) 10
TABLE 15
Phytophthora test (tomato)/protective
Active
compound Effi-
Active compound application cacy
known: rate in g/ha in %
compound of the formula (I)  1 47
Figure US07208510-20070424-C00098
spiroxamine (XI) 10  0
Figure US07208510-20070424-C00099
Mixture according to the invention:
Active Expected value
compound calculated
application Actual using Colby's
Mixing ratio rate in g/ha efficacy formula
(I) 1 47
+ {close oversize brace} 1:10 + {close oversize brace} 86
spiroxamine (XI) 10
TABLE 16
Phytophthora test (tomato)/protective
Active
compound Effi-
Active compound application cacy
known: rate in g/ha in %
compound of the formula (I)  1 39
Figure US07208510-20070424-C00100
fluazinam (XXXI) 10 56
Figure US07208510-20070424-C00101
Mixture according to the invention:
Active
compound Expected value
application Actual calculated using
Mixing ratio rate in g/ha efficacy Colby’s formula
(I) 1 73
+ + {close oversize brace} 87
fluazinam {close oversize brace} 1:10 10
(XXXI)
TABLE 17
Phytophthora test (tomato)/protective
Active
compound Effi-
Active compound application cacy
known: rate in g/ha in %
compound of the formula (I) 1 47
Figure US07208510-20070424-C00102
compound of the formula (XXVIII)(27) 1  9
Figure US07208510-20070424-C00103
Mixture according to the invention:
Active
compound Expected value
application Actual calculated using
Mixing ratio rate in g/ha efficacy Colby's formula
(I) 1 52
+ {close oversize brace} 1:1 + {close oversize brace} 72
(XXVIII) (27) 1
TABLE 18
Phytophthora test (tomato)/protective
Active
compound Effi-
Active compound application cacy
known: rate in g/ha in %
compound of the formula (I) 1 47
Figure US07208510-20070424-C00104
compound of the formula (XIV) (13) 1  8
Figure US07208510-20070424-C00105
Mixture according to the invention:
Active Expected
value
compound calculated
application Actual using Colby's
Mixing ratio rate in g/ha efficacy formula
(I) 1 51
+ {close oversize brace} 1:1 + {close oversize brace} 62
(XIV) (13) 1
TABLE 19
Phytophthora test (tomato)/protective
Active
compound Effi-
Active compound application cacy
known: rate in g/ha in %
formula (I)  1 56
Figure US07208510-20070424-C00106
compound of the formula (XXXXVIa) (40) 50  0
copper oxychloride
Mixture according to the invention:
Expected
Active value calcu-
compound lated using
application Actual Colby's
Mixing ratio rate in g/ha efficacy formula
formula (I) 1 56
+ + {close oversize brace} 82
copper oxychloride {close oversize brace} 1:50 50
(XXXXVIa)
TABLE 20
Phytophthora test (tomato)/protective
Active
compound Effi-
Active compound application cacy
known: rate in g/ha in %
formula (I) 1 56
Figure US07208510-20070424-C00107
compound of the formula (XII) (11) 1 55
azoxystrobin
Figure US07208510-20070424-C00108
Mixture according to the invention:
Expected
Active value calcu-
compound lated using
application Actual Colby's
Mixing ratio rate in g/ha efficacy formula
formula (I) 1 80
+ + {close oversize brace} 95
azoxystrobin (XII) {close oversize brace} 1:1 1
(XXII)
TABLE 21
Phytophthora test (tomato)/protective
Active
compound Effi-
Active compound application cacy
known: rate in g/ha in %
formula (I) 1 56
Figure US07208510-20070424-C00109
compound of the formula (XIII) (12) 1  0
trifloxystrobin
Figure US07208510-20070424-C00110
Mixture according to the invention:
Active
compound Expected value
application Actual calculated using
Mixing ratio rate in g/ha efficacy Colby's formula
formel (I) 1 56
+ + {close oversize brace} 68
trifloxystrobin {close oversize brace} 1:1 1
(XXIII)

Claims (2)

1. An active compound combination comprising at least one compound of formula (I)
Figure US07208510-20070424-C00111
and the tetrachloro-isophthalo-dinitrile of formula (XXIX)
Figure US07208510-20070424-C00112
2. An active compound combination according to claim 1 wherein the weight ratio of the compound of the formula (I) to the compound of the formula (XXIX) is from 1:1 to 1:150.
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PCT/EP2000/011989 WO2001044215A2 (en) 1999-12-13 2000-11-30 Fungicidal combinations of active substances
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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9288996B2 (en) 2010-03-18 2016-03-22 Basf Se Fungicidal compositions comprising a phosphate solubilizing microorganism and a fungicidally active compound
US9867373B2 (en) 2013-05-07 2018-01-16 Jiangsu Huifeng Agrochemical Co., Ltd. Fungicidal composition having synergistic effect

Families Citing this family (38)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19716257A1 (en) 1997-04-18 1998-10-22 Bayer Ag Fungicidal active ingredient combination
UA70327C2 (en) * 1998-06-08 2004-10-15 Баєр Акціенгезельшафт Method of combating phytopathogenic diseases on crop plants and a fungicidal composition
AU2164101A (en) * 1999-12-13 2001-06-25 Bayer Aktiengesellschaft Fungicidal combinations of active substances
BR0206553A (en) * 2001-01-22 2004-06-22 Basf Ag Fungicidal mixtures, method for combating harmful fungi, and fungicidal agent
DE10141618A1 (en) * 2001-08-24 2003-03-06 Bayer Cropscience Ag Fungicidal active ingredient combinations
FR2832031A1 (en) * 2001-11-14 2003-05-16 Aventis Cropscience Sa COMPOSITION FUNGICIDE BASED ON AT LEAST ONE PYRIDYLMETHYLBENZAMIDE DERIVATIVE AND AT LEAST ONE VALINAMIDE-TYPE DERIVATIVE
NZ567862A (en) * 2002-03-21 2009-07-31 Basf Se Fungicidal mixtures comprising prothioconazole and dithianon
DE10228104A1 (en) * 2002-06-24 2004-01-15 Bayer Cropscience Ag Fungicidal active ingredient combination
DE10228103A1 (en) * 2002-06-24 2004-01-15 Bayer Cropscience Ag Fungicidal active ingredient combinations
ES2279170T3 (en) * 2002-07-23 2007-08-16 Basf Aktiengesellschaft FUNGICIDE BLENDS.
GB0227966D0 (en) * 2002-11-29 2003-01-08 Syngenta Participations Ag Organic Compounds
ATE385693T1 (en) * 2004-04-21 2008-03-15 Basf Ag FUNGICIDAL MIXTURES
PE20060796A1 (en) * 2004-11-25 2006-09-29 Basf Ag PROCEDURE TO INTENSIFY THE EFFICIENCY OF ETABOXAM
EP2014167A1 (en) * 2007-07-13 2009-01-14 Bayer CropScience AG Active compound combinations
CN101379983B (en) * 2008-07-04 2011-10-19 张少武 Bactericidal composition containing azoxystrobin and triabendazole and use thereof
AR075573A1 (en) * 2009-02-11 2011-04-20 Basf Se DIMETHOMORPH AS A PESTICIDE PROTECTOR WITH PHYTO-TOXIC EFFECTS
GB0906515D0 (en) 2009-04-15 2009-05-20 Syngenta Participations Ag Fungical compositions
CN101953346B (en) * 2010-09-15 2011-07-20 浙江新农化工股份有限公司 Zinc thiazole-containing bactericidal composition
CN102007917B (en) * 2010-11-09 2013-10-30 浙江农林大学 Composite bactericide and application thereof
US9137997B2 (en) * 2011-04-15 2015-09-22 Basf Se Use of substituted dithiine-dicarboximides for combating phytopathogenic fungi
CN102516267B (en) * 2011-12-06 2015-05-13 西北农林科技大学 Thiodiazole copper compound, and its preparation method, preparation and application
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Citations (66)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1972961A (en) 1931-05-26 1934-09-11 Du Pont Disinfectant
DE610764C (en) 1931-02-04 1935-03-15 Alfred Zschelletzschky Steel-hard, elastic, heat-resistant gold alloy
US2553770A (en) 1948-05-18 1951-05-22 Standard Oil Dev Co Parasiticidal compounds containing the nsccll3 group
US3290353A (en) 1963-04-01 1966-12-06 Diamond Alkali Co Halogenated aromatic nitriles
US3513241A (en) 1966-12-17 1970-05-19 Schering Ag Fungicidal and fungistatic n-(dialkylaminoalkyl) - carbamic acid and thiocarbamic acid esters
DE2012656A1 (en) 1969-03-19 1971-09-30 Sumitomo Chemical Company, Ltd., Osaka (Japan) N- (3,5-dihalophenyl) imides, process for their preparation and their use as microbicides
US3755350A (en) 1970-10-06 1973-08-28 Rhone Poulenc Sa Substituted 3-phenyl hydantoins useful as fungicides
US3823240A (en) 1970-10-06 1974-07-09 Rhone Poulenc Sa Fungicidal hydantoin derivatives
US3903090A (en) 1969-03-19 1975-09-02 Sumitomo Chemical Co Novel n-(3,5-dihalophenyl)-imide compounds
US3912752A (en) 1972-01-11 1975-10-14 Bayer Ag 1-Substituted-1,2,4-triazoles
US3952002A (en) 1973-05-12 1976-04-20 Bayer Aktiengesellschaft Triazolyl-O,N-acetals
US3991071A (en) 1973-06-21 1976-11-09 The Boots Company Limited Fungicidal compositions containing substituted imidazoles
US4009278A (en) 1969-03-19 1977-02-22 Sumitomo Chemical Company, Limited Antimicrobial composition and method containing N-(3,5-dihalophenyl)-imide compounds
US4048318A (en) 1972-01-11 1977-09-13 Bayer Aktiengesellschaft 1-Substituted-1,2,4-triazole fungicides
US4079062A (en) 1974-11-18 1978-03-14 Janssen Pharmaceutica N.V. Triazole derivatives
US4147791A (en) 1972-01-11 1979-04-03 Bayer Aktiengesellschaft 1-Substituted-1,2,4-triazole fungicidal compositions and methods for combatting fungi that infect or attack plants
US4160838A (en) 1977-06-02 1979-07-10 Janssen Pharmaceutica N.V. Antimicrobial and plant-growth-regulating triazole derivatives
US4291049A (en) 1978-02-02 1981-09-22 Montedison S.P.A. Acyl anilines exerting a fungicidal action
US4331670A (en) 1979-12-25 1982-05-25 Ishihara Sangyo Kaisha, Ltd. Pyridylanilines
US4347253A (en) 1980-04-25 1982-08-31 Sandoz Ltd. Fungicides
US4432989A (en) 1980-07-18 1984-02-21 Sandoz, Inc. αAryl-1H-imidazole-1-ethanols
US4457937A (en) 1979-08-16 1984-07-03 Sandoz Ltd. Fungicidal N-substituted phenyl-N-(2-oxo-3-oxazolidinyl)-acetamide derivatives
US4496551A (en) 1981-06-24 1985-01-29 E. I. Du Pont De Nemours And Company Fungicidal imidazole derivatives
US4510136A (en) 1981-06-24 1985-04-09 E. I. Du Pont De Nemours And Company Fungicidal 1,2,4-triazole derivatives
US4532341A (en) 1980-05-16 1985-07-30 Bayer Aktiengesellschaft Oxirane compounds
US4608385A (en) 1981-10-29 1986-08-26 Sumitomo Chemical Company, Limited Fungicidal N-phenylcarbamates
US4664696A (en) 1983-03-04 1987-05-12 Sandoz Ltd. α-phenyl- or benzyl-α-cyclopropylalkylene-1H-imidazole- and 1,2,4-triazole-1-ethanols and use against fungus
US4780551A (en) 1985-06-21 1988-10-25 Ciba-Geigy Corporation Microbicidal compositions
US4851405A (en) 1987-03-07 1989-07-25 Bayer Aktiengesellschaft Aminomethyl heterocyclic compounds
US4910200A (en) 1985-10-09 1990-03-20 Celamerck Gmbh & Co. Kg Acrylic acid morpholides, fungicidal compositions and use
US4920139A (en) 1983-11-10 1990-04-24 Rohm And Haas Company Alpha-alkyl-alpha-(4-halophenyl)-1H-1,2,4-triazole-1-propanenitrile
US4931581A (en) 1987-08-21 1990-06-05 Ciba-Geigy Corporation Process and a composition for immunizing plants against diseases
US4931560A (en) 1987-09-28 1990-06-05 Ciba-Geigy Corporation Pesticides
US4957933A (en) 1989-04-21 1990-09-18 E. I. Du Pont De Nemours And Company Fungicidal oxazolidinones
US4988734A (en) 1988-05-07 1991-01-29 Bayer Aktiengesellschaft Fungicidal stereoisomers of N-(R)-(1-aryl-ethyl)-1-alkyl-2,2,-dichloro-cyclopropanecarboxamides
US4992438A (en) 1986-12-03 1991-02-12 Kumiai Chemical Industry Co., Ltd. Pyrimidine derivatives, process for preparing the same and agricultural or horticultural fungicidal composition containing the same
US4995898A (en) 1987-03-13 1991-02-26 Ishihara Sangyo Kaisha, Ltd. Imidazole compounds and biocidal composition comprising the same for controlling harmful organisms
US5021581A (en) 1987-02-09 1991-06-04 Imperial Chemical Industries Plc Fungicides
US5059623A (en) 1988-04-29 1991-10-22 Bayer Aktiengesellschaft Substituted cycloalkyl- and heterocyclyl-carboxanilides
US5081141A (en) 1986-01-23 1992-01-14 Montedison S.P.A. Fungicidal azolyl-derivatives
US5087635A (en) 1986-07-02 1992-02-11 Rohm And Haas Company Alpha-aryl-alpha-phenylethyl-1H-1,2,4-triazole-1-propanenitriles
US5145843A (en) 1988-01-29 1992-09-08 Dowelanco Quinoline and cinnoline fungicides
US5145856A (en) 1989-02-10 1992-09-08 Imperial Chemical Industries Plc Fungicides
US5153200A (en) 1987-09-28 1992-10-06 Ciba-Geigy Corporation Pesticides
US5221691A (en) 1991-01-30 1993-06-22 Imperial Chemical Industries Plc Fungicides aromatic oxime amides
US5223523A (en) 1989-04-21 1993-06-29 E. I. Du Pont De Nemours And Company Fungicidal oxazolidinones
US5264440A (en) 1989-02-10 1993-11-23 Imperial Chemical Industries Plc Fungicides
US5266585A (en) 1981-05-12 1993-11-30 Ciba-Geigy Corporation Arylphenyl ether derivatives, compositions containing these compounds and use thereof
US5304572A (en) 1992-12-01 1994-04-19 Rohm And Haas Company N-acetonylbenzamides and their use as fungicides
US5334607A (en) 1991-05-28 1994-08-02 Basf Aktiengesellschaft Methods for treating mycoses
US5340802A (en) 1989-06-30 1994-08-23 Abbott Laboratories Peptide analog type-B CCK receptor ligands
US5356908A (en) 1989-04-21 1994-10-18 E. I. Du Pont De Nemours And Company Fungicidal oxazolidinones
US5389308A (en) 1990-09-26 1995-02-14 Buck Werke Gmbh & Co. Composition generating an IR-opaque smoke
US5407902A (en) 1992-10-02 1995-04-18 Mitsubishi Kasei Corporation Methoxyiminoacetic acid derivative and agricultural/horticultural fungicide containing the same as active ingredient
US5453531A (en) 1990-08-25 1995-09-26 Bayer Aktiengesellschaft Substituted valinamide derivatives
EP0775696A1 (en) 1994-08-03 1997-05-28 KumaiI Chemical Industry Co., Ltd. Amino acid amide derivative, process for producing the same, agrohorticultural fungicide, and fungicidal method
US5679676A (en) 1993-08-11 1997-10-21 Bayer Aktiengesellschaft Substituted azadioxacycloalkenes and their use as fungicides
WO1998023155A1 (en) 1996-11-26 1998-06-04 E.I. Du Pont De Nemours And Company Arthropodicidal and fungicidal cyclic amides
US5789430A (en) 1994-11-21 1998-08-04 Bayer Aktiengesellschaft Triazolyl derivatives
US6020354A (en) 1995-08-10 2000-02-01 Bayer Aktiengesellschaft Halobenzimidazoles and their use as microbicides
US6020338A (en) * 1998-02-11 2000-02-01 American Cyanamid Company Fungicidal 7-alkyl-triazolopyrimidines
US6103717A (en) 1996-01-22 2000-08-15 Bayer Aktiengesellschaft Halogen pyrimidines and its use thereof as parasite abatement means
US6130251A (en) 1995-01-30 2000-10-10 Bayer Aktiengesellschaft Alkoximinoacetic acid amides
US6235743B1 (en) 1996-11-11 2001-05-22 Bayer Aktiengesellschaft Halogen pyrimidinyl aryl (thio)ethers as pesticides
US6355634B1 (en) 1990-06-05 2002-03-12 Bayer Aktiengesellschaft Aromatic compounds
US6624183B2 (en) * 1999-12-13 2003-09-23 Bayer Aktiengesellschaft Fungicidal combinations of active substances

Family Cites Families (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NZ179111A (en) * 1974-11-18 1978-03-06 Janssen Pharmaceutica Nv I-(aryl)-ethyl-1h-1,2,4-triazole ketals,anti-microbial and plant growth controlling compositions
JPH0239503B2 (en) * 1981-10-29 1990-09-05 Sumitomo Chemical Co NNFUENIRUKAABAMEETOKEIKAGOBUTSU * SONOSEIZOHOOYOBISOREOJUKOSEIBUNTOSURUNOENGEIYOSATSUKINZAI
JPS58144393A (en) * 1982-02-16 1983-08-27 イ−・アイ・デユポン・デ・ニモアス・アンド・カンパニ− Bactericidal 1,2,4-triazole and imidazole derivatives
CA1227801A (en) * 1983-11-10 1987-10-06 Ted T. Fujimoto .alpha.-ALKYL-.alpha.-(4-HALOPHENYL)-1H-1,2,4-TRIAZOLE-1- PROPANENITRILES
CA1321588C (en) * 1986-07-02 1993-08-24 Katherine Eleanor Flynn Alpha-aryl-alpha-phenylethyl-1h-1,2,4-triazole-1- propanenitriles
JP2606720B2 (en) * 1987-03-13 1997-05-07 石原産業株式会社 Imidazole compounds and pesticides containing them
JPH0692268B2 (en) * 1988-06-03 1994-11-16 日本油脂株式会社 Reduction-reoxidation type semiconductor ceramic capacitor element
DE4026966A1 (en) * 1990-08-25 1992-02-27 Bayer Ag SUBSTITUTED VALINAMIDE DERIVATIVES
AU3127093A (en) * 1991-11-14 1993-06-15 Paul M. Suratt Auto cpap system
DE4304172A1 (en) * 1993-02-12 1994-08-25 Bayer Ag Fungicidal active ingredient combinations
JP3775841B2 (en) * 1995-12-28 2006-05-17 クミアイ化学工業株式会社 Agricultural / horticultural fungicide composition
CA2264528C (en) * 1996-08-30 2007-04-24 Basf Aktiengesellschaft Fungicidal mixtures
WO1998023156A1 (en) * 1996-11-26 1998-06-04 E.I. Du Pont De Nemours And Company Methyl substituted fungicides and arthropodicides
DE19834028A1 (en) * 1998-07-28 2000-02-03 Wolman Gmbh Dr Process for treating wood against infestation by wood-damaging fungi

Patent Citations (96)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE610764C (en) 1931-02-04 1935-03-15 Alfred Zschelletzschky Steel-hard, elastic, heat-resistant gold alloy
US1972961A (en) 1931-05-26 1934-09-11 Du Pont Disinfectant
US2553770A (en) 1948-05-18 1951-05-22 Standard Oil Dev Co Parasiticidal compounds containing the nsccll3 group
US3290353A (en) 1963-04-01 1966-12-06 Diamond Alkali Co Halogenated aromatic nitriles
US3513241A (en) 1966-12-17 1970-05-19 Schering Ag Fungicidal and fungistatic n-(dialkylaminoalkyl) - carbamic acid and thiocarbamic acid esters
US4009278A (en) 1969-03-19 1977-02-22 Sumitomo Chemical Company, Limited Antimicrobial composition and method containing N-(3,5-dihalophenyl)-imide compounds
DE2012656A1 (en) 1969-03-19 1971-09-30 Sumitomo Chemical Company, Ltd., Osaka (Japan) N- (3,5-dihalophenyl) imides, process for their preparation and their use as microbicides
US3745170A (en) 1969-03-19 1973-07-10 Sumitomo Chemical Co Novel n-(3,5-dihalophenyl)-imide compounds
US3903090A (en) 1969-03-19 1975-09-02 Sumitomo Chemical Co Novel n-(3,5-dihalophenyl)-imide compounds
US3755350A (en) 1970-10-06 1973-08-28 Rhone Poulenc Sa Substituted 3-phenyl hydantoins useful as fungicides
US3823240A (en) 1970-10-06 1974-07-09 Rhone Poulenc Sa Fungicidal hydantoin derivatives
US3912752A (en) 1972-01-11 1975-10-14 Bayer Ag 1-Substituted-1,2,4-triazoles
US4048318A (en) 1972-01-11 1977-09-13 Bayer Aktiengesellschaft 1-Substituted-1,2,4-triazole fungicides
US4147791A (en) 1972-01-11 1979-04-03 Bayer Aktiengesellschaft 1-Substituted-1,2,4-triazole fungicidal compositions and methods for combatting fungi that infect or attack plants
US3952002A (en) 1973-05-12 1976-04-20 Bayer Aktiengesellschaft Triazolyl-O,N-acetals
US3991071A (en) 1973-06-21 1976-11-09 The Boots Company Limited Fungicidal compositions containing substituted imidazoles
US4154945A (en) 1973-06-21 1979-05-15 The Boots Company Limited Fungicidal substituted imidazoles
US4079062A (en) 1974-11-18 1978-03-14 Janssen Pharmaceutica N.V. Triazole derivatives
US4160838A (en) 1977-06-02 1979-07-10 Janssen Pharmaceutica N.V. Antimicrobial and plant-growth-regulating triazole derivatives
US4291049A (en) 1978-02-02 1981-09-22 Montedison S.P.A. Acyl anilines exerting a fungicidal action
US4425357A (en) 1978-02-02 1984-01-10 Montedison S.P.A. Acyl anilines exerting a fungicidal action
US4457937A (en) 1979-08-16 1984-07-03 Sandoz Ltd. Fungicidal N-substituted phenyl-N-(2-oxo-3-oxazolidinyl)-acetamide derivatives
US4331670A (en) 1979-12-25 1982-05-25 Ishihara Sangyo Kaisha, Ltd. Pyridylanilines
US4436744A (en) 1980-04-25 1984-03-13 Sandoz Ltd. Fungicidal compositions comprising N-amino-2-oxo-3-oxazolidine derivatives and folpet or captan
US4347253A (en) 1980-04-25 1982-08-31 Sandoz Ltd. Fungicides
US4723984A (en) 1980-05-16 1988-02-09 Bayer Aktiengesellschaft 1-hydroxyethyl-azole compounds and agricultural compositions
US4871390A (en) 1980-05-16 1989-10-03 Bayer Aktiengesellschaft 1-hydroxyethyl-azole compounds and agricultural compositions
US4532341A (en) 1980-05-16 1985-07-30 Bayer Aktiengesellschaft Oxirane compounds
US4626595A (en) 1980-05-16 1986-12-02 Bayer Aktiengesellschaft Oxirane intermediates of 1-hydroxyethyl azole compounds
US4904298A (en) 1980-05-16 1990-02-27 Bayer Aktiengesellschaft 1-Hydroxyethyl-azole compounds and agricultural compositions
US4897107A (en) 1980-05-16 1990-01-30 Bayer Aktiengesellschaft 1-hydroxyethyl-azole compounds and agricultural compositions
US4789672A (en) 1980-05-16 1988-12-06 Bayer Aktiengesellschaft 1-hydroxyethyl-azole compounds and agricultural compositions
US4911746A (en) 1980-05-16 1990-03-27 Bayer Aktiengesellschaft 1-hydroxyethyl-azole compounds and agricultural compositions
US4432989A (en) 1980-07-18 1984-02-21 Sandoz, Inc. αAryl-1H-imidazole-1-ethanols
US5266585A (en) 1981-05-12 1993-11-30 Ciba-Geigy Corporation Arylphenyl ether derivatives, compositions containing these compounds and use thereof
US4510136A (en) 1981-06-24 1985-04-09 E. I. Du Pont De Nemours And Company Fungicidal 1,2,4-triazole derivatives
US4496551A (en) 1981-06-24 1985-01-29 E. I. Du Pont De Nemours And Company Fungicidal imidazole derivatives
US4608385A (en) 1981-10-29 1986-08-26 Sumitomo Chemical Company, Limited Fungicidal N-phenylcarbamates
US4664696A (en) 1983-03-04 1987-05-12 Sandoz Ltd. α-phenyl- or benzyl-α-cyclopropylalkylene-1H-imidazole- and 1,2,4-triazole-1-ethanols and use against fungus
US4849439A (en) 1983-03-04 1989-07-18 Sandoz Ltd. α-phenyl-α-cyclopropylalkyene-1H-imidazole- and 1,2,4 triazole-ethanols as antimycotic agents
US4920139A (en) 1983-11-10 1990-04-24 Rohm And Haas Company Alpha-alkyl-alpha-(4-halophenyl)-1H-1,2,4-triazole-1-propanenitrile
US4925840A (en) 1985-06-21 1990-05-15 Ciba-Geigy Corporation Difluorobenzodioxyl cyanopyrrole microbicidal compositions
US4780551A (en) 1985-06-21 1988-10-25 Ciba-Geigy Corporation Microbicidal compositions
US4910200A (en) 1985-10-09 1990-03-20 Celamerck Gmbh & Co. Kg Acrylic acid morpholides, fungicidal compositions and use
US5081141A (en) 1986-01-23 1992-01-14 Montedison S.P.A. Fungicidal azolyl-derivatives
US5087635A (en) 1986-07-02 1992-02-11 Rohm And Haas Company Alpha-aryl-alpha-phenylethyl-1H-1,2,4-triazole-1-propanenitriles
US4992438A (en) 1986-12-03 1991-02-12 Kumiai Chemical Industry Co., Ltd. Pyrimidine derivatives, process for preparing the same and agricultural or horticultural fungicidal composition containing the same
US5021581A (en) 1987-02-09 1991-06-04 Imperial Chemical Industries Plc Fungicides
US5438059A (en) 1987-02-09 1995-08-01 Zeneca Limited Certain acrylates having fungicidal activity
US4851405A (en) 1987-03-07 1989-07-25 Bayer Aktiengesellschaft Aminomethyl heterocyclic compounds
US4995898A (en) 1987-03-13 1991-02-26 Ishihara Sangyo Kaisha, Ltd. Imidazole compounds and biocidal composition comprising the same for controlling harmful organisms
US4931581A (en) 1987-08-21 1990-06-05 Ciba-Geigy Corporation Process and a composition for immunizing plants against diseases
US5523311A (en) 1987-08-21 1996-06-04 Ciba-Geigy Corporation Process and a composition for immunizing plants against disease
US5190928A (en) 1987-08-21 1993-03-02 Ciba-Geigy Corporation Process and a composition for immunizing plants against diseases
US5153200A (en) 1987-09-28 1992-10-06 Ciba-Geigy Corporation Pesticides
US4997941A (en) 1987-09-28 1991-03-05 Ciba-Geigy Corporation Pesticides
US4931560A (en) 1987-09-28 1990-06-05 Ciba-Geigy Corporation Pesticides
US5145843A (en) 1988-01-29 1992-09-08 Dowelanco Quinoline and cinnoline fungicides
US5240940A (en) 1988-01-29 1993-08-31 Dowelanco Quinoline and cinnoline fungicide compositions
US5059623A (en) 1988-04-29 1991-10-22 Bayer Aktiengesellschaft Substituted cycloalkyl- and heterocyclyl-carboxanilides
US4988734A (en) 1988-05-07 1991-01-29 Bayer Aktiengesellschaft Fungicidal stereoisomers of N-(R)-(1-aryl-ethyl)-1-alkyl-2,2,-dichloro-cyclopropanecarboxamides
US5145856A (en) 1989-02-10 1992-09-08 Imperial Chemical Industries Plc Fungicides
US5264440A (en) 1989-02-10 1993-11-23 Imperial Chemical Industries Plc Fungicides
US5395837A (en) 1989-02-10 1995-03-07 Zeneca Limited Fungicides
US5468747A (en) 1989-02-10 1995-11-21 Zeneca Limited Fungicidal compositions and methods of use employing pyrimidine derivatives
US5223523A (en) 1989-04-21 1993-06-29 E. I. Du Pont De Nemours And Company Fungicidal oxazolidinones
US4957933A (en) 1989-04-21 1990-09-18 E. I. Du Pont De Nemours And Company Fungicidal oxazolidinones
US5356908A (en) 1989-04-21 1994-10-18 E. I. Du Pont De Nemours And Company Fungicidal oxazolidinones
US5340802A (en) 1989-06-30 1994-08-23 Abbott Laboratories Peptide analog type-B CCK receptor ligands
US6355634B1 (en) 1990-06-05 2002-03-12 Bayer Aktiengesellschaft Aromatic compounds
US5453531A (en) 1990-08-25 1995-09-26 Bayer Aktiengesellschaft Substituted valinamide derivatives
US5389308A (en) 1990-09-26 1995-02-14 Buck Werke Gmbh & Co. Composition generating an IR-opaque smoke
US5221691A (en) 1991-01-30 1993-06-22 Imperial Chemical Industries Plc Fungicides aromatic oxime amides
US5342837A (en) 1991-01-30 1994-08-30 Imperial Chemical Industries Plc Fungicides dizinyl oxime ethers
US5334607A (en) 1991-05-28 1994-08-02 Basf Aktiengesellschaft Methods for treating mycoses
US5407902A (en) 1992-10-02 1995-04-18 Mitsubishi Kasei Corporation Methoxyiminoacetic acid derivative and agricultural/horticultural fungicide containing the same as active ingredient
US5304572A (en) 1992-12-01 1994-04-19 Rohm And Haas Company N-acetonylbenzamides and their use as fungicides
US5679676A (en) 1993-08-11 1997-10-21 Bayer Aktiengesellschaft Substituted azadioxacycloalkenes and their use as fungicides
US5883250A (en) 1993-08-11 1999-03-16 Bayer Aktiengesellschaft Substituted azadioxacycloalkenes, fungicidal composition containing them, process for preparing them, and method of using them to combat fungi
US5789428A (en) * 1994-08-03 1998-08-04 Kumiai Chemical Industry Co. Ltd. Amino-acid amide derivatives, processes for preparing the same, agricultural or horticultural fungicides, and method for killing fungi
EP0775696A1 (en) 1994-08-03 1997-05-28 KumaiI Chemical Industry Co., Ltd. Amino acid amide derivative, process for producing the same, agrohorticultural fungicide, and fungicidal method
US5789430A (en) 1994-11-21 1998-08-04 Bayer Aktiengesellschaft Triazolyl derivatives
US5859039A (en) 1994-11-21 1999-01-12 Bayer Aktiengesellschaft Microbicidal triazolyl derivatives
US6130251A (en) 1995-01-30 2000-10-10 Bayer Aktiengesellschaft Alkoximinoacetic acid amides
US6020354A (en) 1995-08-10 2000-02-01 Bayer Aktiengesellschaft Halobenzimidazoles and their use as microbicides
US6127547A (en) 1995-08-10 2000-10-03 Bayer Aktiengesellschaft Halobenzimidazoles and their use as microbicides
US6160001A (en) 1995-08-10 2000-12-12 Bayer Aktiengesellschaft Halobenzimidazoles and their use as microbicides
US6268508B1 (en) 1995-08-10 2001-07-31 Bayer Aktiengesellschaft Halobenzimidazoles and their use as microbicides
US6387939B1 (en) 1995-08-10 2002-05-14 Bayer Aktiengesellschaft Halogenzimidazoles and their use as microbicides
US6103717A (en) 1996-01-22 2000-08-15 Bayer Aktiengesellschaft Halogen pyrimidines and its use thereof as parasite abatement means
US6235743B1 (en) 1996-11-11 2001-05-22 Bayer Aktiengesellschaft Halogen pyrimidinyl aryl (thio)ethers as pesticides
US20010018442A1 (en) 1996-11-11 2001-08-30 Herbert Gayer Halogen pyrimidinyl aryl (thio)ethers as pesticides
US6359133B2 (en) 1996-11-11 2002-03-19 Bayer Aktiengesellschaft Halogen pyrimidinyl aryl (thio) ethers as pesticides
WO1998023155A1 (en) 1996-11-26 1998-06-04 E.I. Du Pont De Nemours And Company Arthropodicidal and fungicidal cyclic amides
US6020338A (en) * 1998-02-11 2000-02-01 American Cyanamid Company Fungicidal 7-alkyl-triazolopyrimidines
US6624183B2 (en) * 1999-12-13 2003-09-23 Bayer Aktiengesellschaft Fungicidal combinations of active substances

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Pesticide Manual, 9<SUP>th </SUP>Ed. (month unavailable) 1991, pp. 206, 249, 431, 443, 461, 491, 529, 531, 554, 654, 726, 827.

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9288996B2 (en) 2010-03-18 2016-03-22 Basf Se Fungicidal compositions comprising a phosphate solubilizing microorganism and a fungicidally active compound
US9867373B2 (en) 2013-05-07 2018-01-16 Jiangsu Huifeng Agrochemical Co., Ltd. Fungicidal composition having synergistic effect

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